HCID 18180288, 화합물 → HCID 18180285, 화합물

HRID 1359021노트

반응식

HRID 1359021 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N+:15]([O-])=O)[CH:6]=[C:7]([O:13][CH3:14])[C:8]=1[O:9][CH2:10][CH2:11][OH:12]>[Pd].C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:6]=[C:7]([O:13][CH3:14])[C:8]=1[O:9][CH2:10][CH2:11][OH:12])[NH2:15]

참가 물질

4

반응물 1

HCID 18180288HCID 18180288, 화합물

생성물 1

HCID 18180285HCID 18180285, 화합물수율 92%

시약·촉매·용매 2

HCID 23938Palladium촉매HCID 702Ethanol용매

실험 절차

A slurry of potassium 2,6-dimethoxy-4-nitrophenolate [Collins, R. P. and Davis, M. J. Chem. Soc. (1961), 1986] (38 g, 160 mmol) in DMF (600 ml) was treated with 2-bromoethanol (25 ml, 353 mmol) and hexamethylphosphorus triamide (31 ml, 176 mmol) and the reaction heated at 115° for 6 h. After cooling, the reaction was poured onto 1M hydrochloric acid (1.5 l) and extracted with ethyl acetate (5×500 ml). The organics were washed with 1M sodium hydroxide (4×700 ml), brine (200 ml) and drfied (MgSO4). Concentration in vacuo gave 3,5-dimethoxy-4-(2-hydroxyethoxy)nitrobenzene as an off white solid (31 g) δH (CDCl3) 7.52 (2H, s), 4.21 (2H, t, J 2.9 Hz), 3.94 (3H, s), 3.76 (2H, m) and 2.94 (1H, br s). MS (ES+) 266 (MNa+, 50%), 244 (MH+, 100%). A mixture of this nitrobenzene (750 mg, 3.16 mmol) and 10% palladium on carbon (75 mg) in ethanol (50 ml) was degassed and then subjected to an atmosphere of hydrogen (balloon) for 16 h. at 200. Dichloromethane was added and the solution filtered and solvent removed in vacuo to give 3,5-dimethoxy-4-(2-hydroxyethoxy)aniline as a grey solid (620 mg) after trituration with diethyl ether. δH (CDCl3+DMSO) 5.84 (2H, s), 3.87-3.84 (2H, m), 3.64 (6H, s) and 3.52-3.49 (2H, m). MS (ES+) 214 (MH+, 100%.

후처리

  1. customwas degassed
  2. additionDichloromethane was added
  3. filtrationthe solution filtered
  4. customsolvent removed in vacuo

출처 및 근거

ORD 기록
ord-b77cf5ce684f4f8f9186d4a3a90fcc34
출처 데이터셋
uspto-grants-2003_07
특허 번호
US06599908B1

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